Decyl(Tri-Tert-Butyl)Phosphonium Tetrafluoroborate/Palladium Acetate: An Effective Catalyst for Cross-Coupling Reaction of Arylbromides with Phenylacetylene in Copper-Free Conditions

2013 ◽  
Vol 188 (1-3) ◽  
pp. 168-170 ◽  
Author(s):  
Vadim Ermolaev ◽  
Vasiliy Miluykov ◽  
Daria Arkhipova ◽  
Elena Zvereva ◽  
Oleg Sinyashin
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Palladium Acetate ◽  
Effective Catalyst ◽  
Tert Butyl ◽  
Cross Coupling Reaction

Room-Temperature, Water-Promoted, Radical-Coupling Reactions of Phenols with tert-Butyl Nitrite

Synlett ◽  
2017 ◽  
Vol 28 (16) ◽  
pp. 2153-2156 ◽  
Author(s):  
Wen-Ting Wei ◽  
Hongze Liang ◽  
Wen-Ming Zhu ◽  
Weida Liang ◽  
Yi Wu ◽  
...  
Keyword(s):  
Room Temperature ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Phenol Derivative ◽  
Tert Butyl ◽  
Radical Coupling ◽  
Air Atmosphere ◽  
Cross Coupling Reaction ◽  
Temperature Water

A radical–radical cross-coupling reaction of phenols with tert-butyl nitrite has been developed with the use of water as an additive. This method allows the construction of C–N bonds under an air atmosphere at room temperature, providing the ortho-nitrated phenol derivative in moderate to good yields.

scholarly journals Hollow-Shell-Structured Mesoporous Silica-Supported Palladium Catalyst for an Efficient Suzuki-Miyaura Cross-Coupling Reaction

Catalysts ◽  
2021 ◽  
Vol 11 (5) ◽  
pp. 582
Author(s):  
Abdulelah Taher Ali Mohammed ◽  
Lijian Wang ◽  
Ronghua Jin ◽  
Guohua Liu ◽  
Chunxia Tan
Keyword(s):  
Chemical Engineering ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Cost Effective ◽  
Active Species ◽  
Palladium Acetate ◽  
Hollow Shell ◽  
Electron Microscopies ◽  
Cross Coupling Reaction ◽  
The Cost

The construction of a high stability heterogeneous catalyst for privileged common catalysis is a benefit in regard to reuse and separation. Herein, a palladium diphenylphosphine-based hollow-shell-structured mesoporous catalyst (HS@PdPPh2@MSN) was prepared by immobilizing bis((diphenylphosphino)ethyltriethoxysilane)palladium acetate onto the inner wall of a mesoporous organicsilicane hollow shell, whose surface was protected by a –Si(Me)3 group. Electron microscopies confirmed its hollow-shell-structure, and structural analyses and characterizations revealed its well-defined single-site active species within the silicate network. As presented in this study, the newly constructed HS@PdPPh2@MSN enabled an efficient Suzuki-Miyaura cross-coupling reaction for varieties of substrates with up to 95% yield in mild conditions. Meanwhile, it could be reused at least five times with good activity, indicating its excellent stability and recyclability. Furthermore, the cost-effective and easily synthesized HS@PdPPh2@MSN made it a good candidate for employment in fine chemical engineering.

scholarly journals Synthesis and Structure of (Nitronyl Nitroxide-2-ido)(tert-butyldiphenylphosphine)gold(I) and -(Di(tert-butyl)phenylphosphine)gold(I) Derivatives; Their Comparative Study in the Cross-Coupling Reaction

Crystals ◽  
2020 ◽  
Vol 10 (9) ◽  
pp. 770
Author(s):  
Igor Zayakin ◽  
Irina Bagryanskaya ◽  
Dmitri Stass ◽  
Maxim Kazantsev ◽  
Evgeny Tretyakov
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Oxidation Potential ◽  
Nitronyl Nitroxide ◽  
X Ray ◽  
Tert Butyl ◽  
Cross Coupling Reaction ◽  
Vis Spectroscopy ◽  
The Cross ◽  
Derivatives Of

We synthesized two new organogold derivatives of a nitronyl nitroxide (NN) with phosphine ligands, namely NN-Au-PtBuPh2 and NN-Au-PtBu2Ph. They were characterized by X-ray diffraction analysis, cyclic voltammetry, and ESR, IR, and UV/Vis spectroscopy. The X-ray structural analysis revealed a tendency of the NN moiety to form a large number of short intermolecular contacts. This phenomenon is related to the anionic nature of the paramagnetic group NN, as evidenced by a significantly lower oxidation potential in comparison with purely organic derivatives of NN radicals. The cross-coupling reaction of NN-Au-PPh3, NN-Au-PtBuPh2, or NN-Au-PtBu2Ph with an activated bromoarene, namely, p-BrC6H4NO2, was investigated. It was shown that regardless of the presence of the bulky tert-butyl substituent, all gold derivatives have similar activities in the cross-coupling reaction and give a cross-coupling product, NN-C6H4NO2, with comparable yields.

scholarly journals Synthesis of Mono- and Bis-Pyrazoles Bearing Flexible p-Tolyl Ether and Rigid Xanthene Backbones, and Their Potential as Ligands in the Pd-Catalysed Suzuki–Miyaura Cross-Coupling Reaction

Catalysts ◽  
2019 ◽  
Vol 9 (9) ◽  
pp. 718
Author(s):  
Zahid Hussain ◽  
Cristiane Schwalm ◽  
Raoní Rambo ◽  
Renieidy Dias ◽  
Rafael Stieler ◽  
...  
Keyword(s):  
Catalytic System ◽  
Good Yield ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Boronic Acids ◽  
Aryl Halides ◽  
Tert Butyl ◽  
Cross Coupling Reaction ◽  
Ullmann Coupling

The present work describes the synthesis of mono- and bis-pyrazole compounds bearing flexible p-tolyl ether and rigid 4,5-dibromo-2,7-di-tert-butyl-9,9-dimethyl-9H-xanthene backbones as pyrazolyl analogues of DPEphos and Xantphos ligands, respectively. The synthesis of new pyrazolyl analogues was accomplished following an Ullmann coupling protocol, and the resulting products were isolated in overall good yields. In addition, a hybrid imidazolyl–pyrazolyl analogue bearing a xanthene backbone was synthesized using the same protocol, whereas a hybrid selanyl–pyrazolyl analogue with a xanthene backbone was synthesized in a good yield employing a second C–H activation step. The symmetrical bis-pyrazolyl and the hybrid imidazolyl–pyrazolyl analogues were found to be the most active among the new ligands evaluated in the Pd-catalysed Suzuki-Miyaura cross-coupling of aryl halides with aryl boronic acids. A simple catalytic system based on Pd(OAc)2/2a was developed, which efficiently catalyses the Suzuki–Miyaura reaction of aryl halides and aryl boronic acids and provides moderate to excellent yields of the corresponding cross-coupling products.

Synthesis and characterization of trinuclear N-heterocyclic carbene–palladium(ii) complexes and their applications in the Suzuki–Miyaura cross-coupling reaction

RSC Advances ◽  
2016 ◽  
Vol 6 (103) ◽  
pp. 100690-100695 ◽  
Author(s):  
Tao Wang ◽  
Lantao Liu ◽  
Kai Xu ◽  
Huanping Xie ◽  
Hui Shen ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Synthesis And Characterization ◽  
Effective Catalyst ◽  
Cross Coupling Reaction ◽  
One Step

Five novel trinuclear N-heterocyclic carbene–palladium(ii) complexes 5a–e were conveniently synthesized in one step. The obtained palladium(ii) complexes were the effective catalyst precursors for the Suzuki–Miyaura coupling.

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